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Fall & Winter Hikes, Runs & Walks In The Huntington /Five Harbors Area

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Fall & Winter Hikes, Runs & Walks On Long Island

Get out, get fit and enjoy beautiful surrounding at these runs and walks in Huntington Township and the communities surrounding it .

Fall 

Check back for Fall 2025 hikes & runs

Fall 2025 Runs 

9/6Smith Point Bridge 5k Run/Walk for Literacy

9/7 - Whit Whit Walk - Caumsett State Park in Lloyd Harbor - a family-friendly 5K walkathon that supports Pediatric Cancer research at Memorial Sloan Kettering Cancer Center (MSK). Since its inception in 2012, the Whit Whit Fund has raised more than $1,400,000 to find more effective and less toxic treatments for children with cancer.

9/13- Half-Way to St. Patrick's Day 5K & Little Leprechauns Fun Run  

9/14 - Girl Scouts of Nassau County Thin Mint Sprint 5K - Join for the inaugural Thin Mint Sprint 5k Run and Family Fun 1-mile Walk on at Jones Beach State Park. Families and avid runners of all ages are invited to join on Girl Scouts Love State Parks Weekend for the first ever Girl Scout cookie-themed fun run and activity fair.

9/20- Great Cow Harbor 10K Run& 2K Fun Run/Walk- Northport-  Great Cow Harbor 10K Run is one of the most prestigious foot races in the country. Runner's World has named the Great Cow Harbor 10K Run as one of the top 100 races in the USA. New England Runner regularly places The Great Cow Harbor 10K Run in its Top 100 Races, stating "Big race atmosphere in a small town on the Island; it's a winner! Who says those "rolling" courses can't be fun?" The 2K Fun Run / Walk has been a huge success.

9/21 - 5K & Paws Walk - Belmont Lake State Park - benefitting Baxter's Pantry at Long Island Cares

9/27- St. Vincent de Paul of Long island Friends of the Poor Walk/Run  

9/27 - America Vet Dog Annual 5K Run & Dog Walk - Smithtown

TBD- Smithtown Running of the Bull 1K Fun Run & 5K- Proceeds from the run are in part to benefit Angela’s House for Technology-Dependent Children - Run organizers ask that all runners bring a food item for the Smithtown Food Pantry.

10/18 - Town of Oyster Bay Supervisor's 5k Run/Walk 

10/18 - Post Office Cafe Annual Race for MPS-  raise awareness and funds for the National MPS Society. 

10/18 & 10/19- Catholic Health Services Suffolk County Marathon/Half Marathon

10/19 -   Michael Sena's Run for Hope - all proceeds go to the Michael Sena Memorial Fund, Inc a 501(c)(3) public  charity focused on raising awareness about drug addiction, while sharing knowledge and resources for those battling addiction and their families.  

10/26- The John Theissen Children's Foundation Freaky 5k and Walk and Kids Trick or Treat trot 1/4 mile fun run- Wantagh

10/25- Greenlawn Fire Department Annual Halloween 5K Run-  Run the fast and flat 5k course through the town of Greenlawn beginning and ending at the Greenlawn Fire Department's Headquarters. 

11/9- Nassau County 5k & 10k Turkey Trot- proceeds go to INN (Interfaith Nutrition Network)

11/27Townwide Fund - Thanks4giving Run

TBD- Blue Point Turkey Trot  - 5K Fun Run with proceeds going to help the youth on LI

11/22 - The Neil Chadderton Memorial EisnerAmper 4 Mile Race to Feed LI

11/27- Oyster Bay Turkey Trot 5K By the Bay- The Longest Consecutive Turkey Trot in the Tri-State

12/6- Annual Seaford Wellness Hot Chocolate 5K Run/Walk - All proceeds from this community event are used specifically for programs in Seaford

12/14- Jingle All The Way 5K - athletes are encouraged to  bring a new unwrapped toy for sick and underprivileged children across Long Island to the race. All toys go to the John Theissen Children's Foundation Annual Toy Drive www.jtcf.org

Leaf Peeping & Top Hiking Locations

Cold Spring Harbor State Park

Cold Spring Harbor

Caumsett State Park

Lloyd Neck

Nassau-Suffolk Greenbelt Trail

Massapequa to Cold Spring Harbor

Prosser Pines

Middle Island


Winter 2026

Details are still to be determined- check back in December

1st Day Hikes & Run - 2026

1/1 CSH Fish Hatchery: New Year's Day Hike
1/1  LI Greenbelt Trail Conference: Hither Woods New Year's Hike

1/1 NYS Parks Dept Hosted 1st Day Hikes on Long Island:
-Caumsett State Park
-Bethpage State Park
-Shirley Chrisholm State Park
-Jones Beach State Park
-Connetquot River State Park Preserve
-Sunken Meadow State Park
-Ridge Conservation Area
-Hallock State Park Preserve
-Montauk Point State Park

Seal Walks 2026 

Best time to see Seals on LI is typically March

NYS Parks
Montauk & Jones Beach locations

 

For more great runs & hikes... 

Northport Running Club - coordinates runs and events through the year.

Greater Long Island Running Club (GLIRC)- hosts runs across Long Island. 

Long Island Greenbelt Conference - unique, non profit grassroots org that has created more than 200 miles of hiking path on LI & more. 

Run.LI - a portal dedicated to Long Island runners. 

NYS Winter Run Series - various runs throughout state parks 

EventPower Empower Youself- empowerment events, runs and races

Strong island Running Club  

 Educational Walks & Hikes

Check event websites for details and additional Events

North Shore Land Alliance

NYS Parks

Sands Point Preserve

Sweet Briar Nature Center